Water → N-(2-aminoethyl)-8-dimethylamino-6,6-diphenyl-5-hydroxynonylamine

HRID 1461150Notes

Reaction equation

HRID 1461150 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[CH3:5][N:6]([CH3:30])[CH:7]([CH2:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16])[CH:8]=O.C([BH3-])#N.[Na+].O>CO>[NH2:3][CH2:2][CH2:1][NH:4][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]([OH:17])[C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:10][CH:7]([N:6]([CH3:30])[CH3:5])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 3301EthylenediamineHCID 5003444Sodium cyanoborohydrideHCID 199815072-Dimethylamino-4,4-diphenyl-5-oxononanal

Product 1

HCID 19981504N-(2-aminoethyl)-8-dimethylamino-6,6-diphenyl-5-hydroxynonylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethylenediamine was added to a solution of 2-dimethylamino-4,4-diphenyl-5-oxononanal (12 mg), as prepared in Example 1, in methanol (0.5 ml). After the mixture was stirred at room temperature, sodium cyanoborohydride (10 mg) was added. The mixture was stirred at room temperature for 18 hours, water was added, and the aqueous mixture was extracted with chloroform. The combined extracts were washed with brine and dried (MgSO4). Rotary evaporation gave a crude product which was further dried in vacuo to yield 4 mg of N-(2-aminoethyl)-8-dimethylamino-6,6-diphenyl-5-hydroxynonylamine.

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. extractionthe aqueous mixture was extracted with chloroform
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customRotary evaporation
  6. customgave a crude product which
  7. customwas further dried in vacuo

Sources & evidence

ORD record
ord-2e4f68c48f8b4e7ca52b97dcfd833cdb
Source dataset
uspto-grants-1991_12
Patent number
US05073629

Reaction notes

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